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Adenophostin

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Adenophostin A
Names
IUPAC name oxy]-5-(hydroxymethyl)-3-tetrahydrofuranyl] dihydrogen phosphate
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
IUPHAR/BPS
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H26N5O18P3/c17-13-7-14(19-3-18-13)21(4-20-7)15-12(39-42(31,32)33)9(5(1-22)34-15)36-16-8(24)11(38-41(28,29)30)10(6(2-23)35-16)37-40(25,26)27/h3-6,8-12,15-16,22-24H,1-2H2,(H2,17,18,19)(H2,25,26,27)(H2,28,29,30)(H2,31,32,33)/t5-,6-,8-,9-,10-,11-,12-,15-,16-/m1/s1Key: RENVITLQVBEFDT-MZQFDOALSA-N
  • InChI=1/C16H26N5O18P3/c17-13-7-14(19-3-18-13)21(4-20-7)15-12(39-42(31,32)33)9(5(1-22)34-15)36-16-8(24)11(38-41(28,29)30)10(6(2-23)35-16)37-40(25,26)27/h3-6,8-12,15-16,22-24H,1-2H2,(H2,17,18,19)(H2,25,26,27)(H2,28,29,30)(H2,31,32,33)/t5-,6-,8-,9-,10-,11-,12-,15-,16-/m1/s1Key: RENVITLQVBEFDT-MZQFDOALBO
SMILES
  • O=P(O)(O)O4(O1O((OP(=O)(O)O)(OP(=O)(O)O)1O)CO)(O4n2c3ncnc(N)c3nc2)CO
Properties
Chemical formula C16H26N5O18P3
Molar mass 669.32 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Adenophostin A is a potent inositol trisphosphate (IP3) receptor agonist, but is much more potent than IP3.

IP3R is a ligand-gated intracellular Ca release channel that plays a central role in modulating cytoplasmic free Ca concentration (Cai). Adenophostin A is structurally different from IP3 but could elicit distinct calcium signals in cells.

References

  1. Mak, D.-O. D.; McBride, S; Foskett, JK (2001). "ATP-dependent Adenophostin Activation of Inositol 1,4,5-Trisphosphate Receptor Channel Gating: Kinetic Implications for the Durations of Calcium Puffs in Cells". The Journal of General Physiology. 117 (4): 299–314. doi:10.1085/jgp.117.4.299. PMC 2217258. PMID 11279251.
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